# US 5,348,986 A · Photocurable silicone composition, and method of making same

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- Number: US 5,348,986 A
- Document ID: US5348986A
- Status: Granted
- Kind: A
- Application number: 08/007,946
- Filed: 1993-01-25
- Granted: 1994-09-20
- Earliest claimed: 1990-11-19
- Assignees: Loctite Corporation
- Inventors: Hsien-Kun Chu; Robert P. Cross; David I. Crossan; Edward K. Welch, II
- Web page: https://patentgrep.com/patent/US5348986A

## CPC

- C08L 83/14: in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms (C08L83/10 takes precedence)
- C08G 77/50: by carbon linkages
- C09D 183/14: in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms (C09D183/10 takes precedence)
- C09K 3/1018: {Macromolecular compounds having one or more carbon-to-silicon linkages}
- C09K 2003/1062: {UV-curable materials}
- C09K 2200/0247: Silica
- C09K 2200/0625: Polyacrylic esters or derivatives thereof
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

Photocurable silicone compositions based on capping of a silicone with a silyl diacrylate capper of the formula ##STR1## wherein: R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, and R .sub.10 are independently selected from hydrogen, halo, and organo radicals; and n is an integer having a value of from 1 to 4. In specific embodiments, the compositions include a polymodal-cure resin composition comprising an acryloxy-functional capped silicone, and a photocurable silicone gel composition and precursor thereof.

## Claims

### Claim 1

A silicone:
(i) capped, by a non-hydrolysis capping reaction, with acryloxy functional moieties of a silyl diacrylate caper of the formula: ##STR36## wherein: R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 R.sub.7, R.sub.8, R.sub.9, and R.sub.10 are independently selected from hydrogen, halo, and organo radicals; and n is an integer having a value of from 1 to 4;
whereby said silicone is partially curable under radiation exposure conditions curingly effective therefor, optionally including the presence therewith of a photoinitiator, and
(ii) having additional functionality imparting to the silicone at least one partial curing modality different from the partially curingly effective radiation exposure conditions constituting a first partial curing modality therefor, or
being present with another material which is curable by curing conditions other than actinic radiation exposure curingly effective for the silicone by virtue of the acryloxy-functional moieties thereof.

### Claim 2 (depends on 1)

A silicone according to claim 1, of the formula: ##STR37## wherein: each R is independently selected from the group consisting of hydrogen, halo, and organo radicals;
each X is independently:
(i) an acryloxy-functional capping moiety derived from said silyl diacrylate capper and imparting actinic radiation exposure curability, optionally in the presence of a photoinitiator, to the silicone, or
(ii) an additional function moiety imparting to the silicone another cure modality differing form its actinic radiation exposure curability by virtue of acryloxy-functional moieties thereof;
each of a,b,c, and d is independently 0, 1, 2, or 3;
s is 0 or a positive integer; and
t is a positive integer;
provided that:
(a+b)=(c+d)=3;
(b+d+s)is greater than or equal to 2; and
the equivalents ratio of acryloxysilyl functionality to said additional functionality (ii) is selected from the group consisting of:
(A) an equivalents ratio of from 0.1:0.9 to 0.8:0.2; and
(B) 0.1:0.9 to 1.0:0.0, when the silicone is present with another material which is curable by curing conditions other than actinic radiation exposure curingly effective for the silicone by virtue of the acryloxy-functional moieties thereof.

### Claim 3 (depends on 2)

A silicone according to claim 2, wherein each R is independently selected from C.sub.1 -C.sub.8 alkyl, and phenyl.

### Claim 4 (depends on 2)

A silicone according to claim 2, wherein each R is methyl.

### Claim 5 (depends on 2)

A silicone according to claim 2, wherein s is less than 20.

### Claim 6 (depends on 2)

A silicone according to claim 2, wherein s is less than 8.

### Claim 7 (depends on 2)

A photocurable composition comprising a silicone according to claim 2, and a photoinitiator.

### Claim 8 (depends on 7)

A photocured product formed by exposure of the photocurable composition of claim 7 to radiation exposure conditions curingly effective therefor.

### Claim 9 (depends on 8)

A cured silicone formed by subjecting the photocured silicone composition of claim 8 to additional curing conditions further curingly effective therefor to produce a fully cured silicone composition.

### Claim 10 (depends on 1)

A silicone according to claim 1, comprising a photocurable silicone gel composition formed as a reaction product of:
(a) a first silane of the formula: ##STR38## wherein: R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, and R.sub.10 are independently selected from hydrogen, halo, and organo radicals; and
n is an integer having a value of from 1 to 4;
(b) a second silane of the formula: ##STR39## wherein: R.sub.11 and R.sub.16 are non-polymerizable groups and are independently selected from halo and organo radicals;
R.sub.12, R.sub.13, R.sub.14, and R.sub.15 are independently selected from hydrogen, halo, and organo radicals; and
n is an integer having a value of from 1 to 4; and
(c) a polysiloxane having at least two functional groups per molecule with which said first and second silanes are cappingly and non-hydrolyzingly reactive;
wherein: (1) the first and second silanes together are provided in sufficient quantity relative to said polysiloxane to non-hydrolyzingly react with substantially all of the cappingly reactive functional groups of the polysiloxane, and (2) the first silane constitutes from about 50% to about 98% by weight of the total weight of the first and second silanes.

### Claim 11 (depends on 10)

A composition according to claim 10, wherein the reaction is carried out at a temperature of from about 0.degree. C. to about 100.degree. C.

### Claim 12 (depends on 10)

A composition according to claim 10, wherein the reaction is carried out at room temperature.

### Claim 13 (depends on 10)

A composition comprising a photocurable silicone gel composition according to claim 10, and an effective amount of a photoinitiator for curing of said photocurable silicone gel composition under radiation exposure curing conditions.

### Claim 14 (depends on 13)

A composition according to claim 13, wherein the photoinitiator comprises a material selected from the group consisting of benzophenone, benzoin, acetophenone, benzil, and their substituted forms, and mixtures thereof.

### Claim 15 (depends on 13)

A composition according to claim 13, wherein the photoinitiator comprises diethoxyacetophenone.

### Claim 16 (depends on 13)

A composition according to claim 13, further comprising a filler.